Acetic Acid → HCID 117841019, compound

HRID 714892Notes

Reaction equation

HRID 714892 reaction equation
Cl[C:2]1[N:7]=[C:6]([N:8]2[CH2:12][CH2:11][C:10]([CH:15]3[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]3)([C:13]#[N:14])[C:9]2=[O:26])[CH:5]=[CH:4][N:3]=1.[O:27]1[CH2:32][CH2:31][N:30]([C:33]2[CH:39]=[CH:38][C:36]([NH2:37])=[CH:35][CH:34]=2)[CH2:29][CH2:28]1.C(O)(=O)C>C(O)CCC>[C:13]([C:10]1([CH:15]2[CH2:18][N:17]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[CH2:16]2)[CH2:11][CH2:12][N:8]([C:6]2[CH:5]=[CH:4][N:3]=[C:2]([NH:37][C:36]3[CH:35]=[CH:34][C:33]([N:30]4[CH2:31][CH2:32][O:27][CH2:28][CH2:29]4)=[CH:39][CH:38]=3)[N:7]=2)[C:9]1=[O:26])#[N:14]

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 75655Benzenamine, 4-(4-morpholinyl)-HCID 117839931HCID 117839931, compound

Product 1

HCID 117841019HCID 117841019, compoundYield 25.5%

Reagents, catalysts & solvents 1

HCID 2631-ButanolSolvent

Procedure

A solution of tert-butyl 3-(1-(2-chloropyrimidin-4-yl)-3-cyano-2-oxopyrrolidin-3-yl)azetidine-1-carboxylate (100 mg) obtained in Step D of Example 309, 4-morpholinoaniline (61 mg) and acetic acid (50 μL) in n-butanol (4.0 mL) was stirred in a microwave reactor at 150° C. for 1 hr, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate), and recrystallized (diisopropyl ether/ethyl acetate) to give the title compound (35 mg).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. customThe residue was purified by silica gel column chromatography (NH, hexane/ethyl acetate)
  3. customrecrystallized (diisopropyl ether/ethyl acetate)

Sources & evidence

ORD record
ord-a0156fc3a76a44428a5b77908a7882aa
Source dataset
uspto-grants-2015_11
Patent number
US09187453B2

Reaction notes

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